Experience the Windy City while you #stayathome

When not covered in oodles of snow, Chicago is one beautiful city, with one of the best skylines in the world, to soak up the sun. Given the coronavirus-imposed quarantine, it may not be an option this year, but these shows and movies take you straight to Lake Michigan and Millennium Park.

Movies on Netflix, Amazon Prime Video and YouTube based in Chicago

Ferris Bueller’s Day off (Netflix)

Ferris convinces his entire school he’s at death’s door and then hits the streets of Chicago with his girlfriend and best friend for a day of fun. This one will get you all nostalgic about the city—be it Ferris and Cameron heckling at Wrigley Field, the gang heading to the Art Institute of Chicago, or the infamous parade sequence. John Hughes shot the movie nearly as a love letter to Chicago, the city in which he was raised.

The Untouchables (Netflix)

Al Capone, a gangster in Chicago, has been the subject of many movies, but Brian De Palma’s crime drama is the best depiction of the city’s most infamous episode. This Oscar winner would be an iconic entry for its Union Station scene alone, but people often forget how much the movie utilised the rest of Chicago. From meetings on Michigan Avenue Bridge to Sean Connery’s famous speech on the Chicago Way (shot at Our Lady of Sorrows Basilica on West Jackson Boulevard), The Untouchables is literally a tour of the city: the Chicago Cultural Center, Blackstone Hotel, the Chicago Theater, City National Bank and Trust Company Building, and so much more.

My Best Friend’s Wedding (Netflix)

Watch Julia Roberts as she dashes to and from O’Hare to the home of the White Sox, to the El and, of course, Fourth Presbyterian Church on East Chestnut Street. While Roberts’ character realises too late that she’s in love with her longtime pal who’s about to tie the knot, the 1997 classic highlights the vibrance of Chicago like no other.

The Break-Up (Netflix)

In The Break-Up, Vince Vaughn portrays an obnoxious owner of a Chicago-based tour company who ill treats his live-in girlfriend (Jennifer Aniston) and later is oblivious to why she breaks up with him. They share a lovely Downtown condo that neither of them can afford on their own, and the pair get into a battle of wits to force the other to move out first. Starting from the iconic Wrigley Field to shots of the skyline and Michigan Avenue, the movie has phenomenal Chicago scenery just rolling. Bonus points for showing the city in all its winter glory.

The Home Alone series (YouTube)

Few movies can be identified more with the Chicago suburbs than the massive holiday hit that turned Macaulay Culkin into a household name. Shot mostly in Winnetka, 25km north of Downtown Chicago, Home Alone captures the northern suburbs while also taking a quick trip to a church in Oak Park. It’s hard to imagine the holiday season without thinking of poor Kevin McCallister.

Shows on Amazon Prime Video to experience Chicago

Chicago Med

An emotional journey through the day-to-day chaos of Chicago’s newest state-of-the-art trauma center and into the lives of its courageous doctors, nurses and staff. Together, they take on the city’s most critical cases and challenges while dealing with personal and interpersonal issues. The shows’ heavy use of locations for shoots casts the city in great light and makes you want to watch more.

Shameless

Adapted from the eponymous British series, this drama about the deeply dysfunctional, rough-and-tumble Gallagher clan is Showtime TV network’s longest-running scripted series. Frank Gallagher is the head of a working-class family in Chicago. His six children bear the brunt of his heavy drinking, and Fiona, the eldest daughter, has to look after everyone.